Trying to put myself in your position, is rather hard as I'm 69 and becoming recoil sensitive. And yet I'm shooting/sighting in my friends 30-06...and surviving. He also has a 300 Weatherby Magnum to sight in, but not by me!
LR involves a lot of shooting to be good at it, which means the caliber has to be fun/enjoyable to shoot...AND...somewhat economical as well. I would ask myself, what caliber do the LR professionals shoot? I don't know any pro LR shooters per sie, but I do follow Erik Cortina, who is. He shoots a 6.5 x 47 Lapua. This recoil will allow you plenty of enjoyable, economical shooting while developing an accurate load. Here are some steps I would do if I was going LR:
1)...pick a known accurate caliber (a 6.5x47 Lapua might do nicely), that's economical in a rifle package you can carry in the woods, since hunting is your major goal, not bench rest shooting per sie, but you'll do plenty of this along the way.
2)...pick your elk killing bullet...NOW...your focus should be getting your rifle, scope, bullet, powder, brass, & primer to shoot as one.
2)...DO NOT SKIMP on a scope! Rule of thumb...a $1500 rifle deserves a $1500 scope. You can't hit what you can't see.
3)...upgrade your minimal knowledge of reloading to just the particular caliber you'll be shooting...it will take the rest of your life to learn the rest of reloading.
4)...DO NOT SKIMP on your bench rest shooting platform. Your focus should be getting your rifle/load to shoot as one. Eliminate as much of 'you' as possible when developing your shooting groups, so when you miss that elk at 800 yards, it won't the rifle/load's fault.
5)...focus shooting at 100 yards...PRACTICE-PRACTICE-PRACTICE...until you can shoot out the eye of a woodchuck at 100 yards. (Because if you can't, you'll be useless at 1000 yards.)
6)...move to a 200 yard range, focusing on shooting 1/4" MOA groups (1/2" groups at this point).
7)...never move to the next 100 yard range until you've mastered the previous one. Jumping from a 100 yard range to a 500 yard range will bring in many problems that would have been eliminated by going through each 100 yard step systematically. (In other words, it doesn't pay to cheat!) Besides, moving through the 100 yard steps helps the learning needed for the bullet drop/windage adjustments.
, 8)...so you've reached the 1000 yard target...CONGRADULATIONS...you should be shooting 2.50" groups at 1000 yards...MAYBE...there's many variables between muzzle/1000 yards...BUT...if you can do 2.50" consistently, skip elk hunting, go PRO!
I know some of this is common knowledge, and can be ignored. But if I mentioned something that did tripped a trigger, then this was worth it!
Above all...make it a fun & enjoyable adventure!